607-28-3Relevant academic research and scientific papers
Molecular modeling and in vitro studies of a neutral oxime as a potential reactivator for acetylcholinesterase inhibited by paraoxon
de Paula, Reuel L.,de Almeida, Joyce S.F.D.,Cavalcante, Samir F.A.,Gon?alves, Arlan S.,Simas, Alessandro B.C.,Franca, Tanos C.C.,Valis, Martin,Kuca, Kamil,Nepovimova, Eugenie,Granjeiro, José M.
, (2018)
The present work aimed to compare the small, neutral and monoaromatic oxime, isatin-3-oxime (isatin-O), to the commercial ones, pralidoxime (2-PAM) and obidoxime, in a search for a new potential reactivator for acetylcholinesterase (AChE) inhibited by the pesticide paraoxon (AChE/POX) as well as a novel potential scaffold for further synthetic modifications. The multicriteria decision methods (MCDM) allowed the identification of the best docking poses of those molecules inside AChE/POX for further molecular dynamic (MD) studies, while Ellman’s modified method enabled in vitro inhibition and reactivation assays. In corroboration with the theoretical studies, our experimental results showed that isatin-O have a reactivation potential capable of overcoming 2-PAM at the initial moments of the assay. Despite not achieving better results than obidoxime, this molecule is promising for being an active neutral oxime with capacity of crossing the blood–brain barrier (BBB), to reactivate AChE/POX inside the central and peripheral nervous systems. Moreover, the fact that isatin-O can also act as anticonvulsant makes this molecule a possible multipotent reactivator. Besides, the MCDM method showed to be an accurate method for the selection of the best docking poses generated in the docking studies.
Pronounced ionic liquid effect in the synthesis of biologically active isatin-3-oxime derivatives under acid catalysis
Pinto, Angelo C.,Lapis, Alexandre A. Moreira,da Silva, Barbara Vasconcellos,Bastos, Renato S.,Dupont, Ja?rton,Neto, Brenno A.D.
, p. 5639 - 5641 (2008)
An efficient method was developed for the preparation of isatin-3-oxime derivatives with Bronsted and/or Lewis acids in imidazolium-based ionic liquids. Isatin-3-oxime bearing the electron donating methoxy group was equally obtained in good yields. The pr
The benzonitrile derivative
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Paragraph 0048-0049, (2021/10/08)
[A] suppressing the generation of impurities caused by side reactions and reaction, and benzonitrile derivative can be obtained in high purity of the benzonitrile derivative method. The compound represented by general formula [a] I, III and IV compound represented by general formula compound represented by a general formula selected from the group consisting of tertiary amines in the presence of at least 1 species is reacted, the benzonitrile derivative represented by general formula II comprises obtaining the benzonitrile derivative. In the general formula I, R1 - R4 Each independently, a hydrogen atom, an alkyl group of carbon number 1 - 5 represent the like, in the general formula II, R21 - R24 Each independently, a hydrogen atom, an alkyl group of carbon number 1 - 5 represent the like, in the general formula III, R31 - R33 Is, each independently represents an alkyl group or a phenyl group, having the general formula IV in, R41 - R44 Is, each independently represents an alkyl group. The details of the code as described herein. [Drawing] no
Synthesis and evaluation of isatin derivatives as antifungal agents
Dawar, Monika,Kaur, Komalpreet,Rani, Ritu,Utreja, Divya
, p. 199 - 205 (2020/02/29)
Various types of isatin derivatives were synthesized by reacting isatin with different reagents viz substituted acetophenones, sodium nitrate, hydroxylamine hydrochloride and hydrazine hydrate. Characterization of the synthesized compounds was done by using various spectral techniques such as IR,1HNMR,13CNMR, elemental analysis and mass spectrometry. Synthesized compounds were further evaluated for their antifungal activity against Helminthosporium oryzae, Rhizoctonia solani and Fusarium moniliforme using poison food technique. 3-(2-Oxo-2-phenylethylidene) indolin-2-one showed significant mycelium inhibition against all tested rice fungi.
1,3-Dipolar Cycloaddition of 3-Amino Oxindole-Based Azomethine Ylides and O-Vinylphosphonylated Salicylaldehydes for Diastereoselective Synthesis of Oxindole Spiro-P, N-polycyclic Heterocycles
Huang, Tiao,Kong, Dulin,Liu, Li,Wang, Qinghe,Wu, Mingshu
supporting information, p. 1387 - 1397 (2020/04/27)
An efficient stereoselective assembly strategy for the construction of pyrrolidin-2,3′-oxindole cis-fused phosphadihydrocoumarins was established. The process involves the condensation of O-vinylphosphonylated salicylaldehydes and 3-amino oxindoles followed by intermolecular cycloaddition with high diastereoselectivity and atom economy.
Synthesis and in vitro evaluation of neutral aryloximes as reactivators of Electrophorus eel acetylcholinesterase inhibited by NEMP, a VX surrogate
Cavalcante, Samir F. de A.,Kitagawa, Daniel A.S.,Rodrigues, Rafael B.,Bernardo, Leandro B.,da Silva, Thiago N.,dos Santos, Wellington V.,Correa, Ana Beatriz de A.,de Almeida, Joyce S.F.D.,Fran?a, Tanos C.C.,Ku?a, Kamil,Simas, Alessandro B.C.
, (2019/06/24)
Casualties caused by nerve agents, potent acetylcholinesterase inhibitors, have attracted attention from media recently. Poisoning with these chemicals may be fatal if not correctly addressed. Therefore, research on novel antidotes is clearly warranted. Pyridinium oximes are the only clinically available compounds, but poor penetration into the blood-brain barrier hampers efficient enzyme reactivation at the central nervous system. In searching for structural factors that may be explored in SAR studies, we synthesized and evaluated neutral aryloximes as reactivators for acetylcholinesterase inhibited by NEMP, a VX surrogate. Although few tested compounds reached comparable reactivation results with clinical standards, they may be considered as leads for further optimization.
Copper-Catalyzed Carbonyl Group Controlled Coupling of Isatin Oximes with Arylboronic Acids To Prepare N-Aryloxindole Nitrones
Mo, Xue-Ling,Chen, Chun-Hua,Liang, Cui,Mo, Dong-Liang
, p. 150 - 159 (2017/11/28)
A variety of (E)-N-aryloxindole nitrones were prepared in good to excellent yields by using a copper-catalyzed coupling reaction of isatin oximes and arylboronic acids under mild conditions. Various arylboronic acids that contain sensitive functional groups were tolerated in the transformation, and detailed studies show that the carbonyl group of the isatin oximes serves as a ligand to control the formation of the (E)-oxindole nitrones. This method to prepare (E)-N-aryloxindole nitrones was easily performed on a gram scale and efficiently used to synthesize estrone-derived oxindole nitrone in high yield.
Synthesis of N-Aryl Oxindole Nitrones through a Metal-Free Selective N-Arylation Process
Wu, Si-Yi,Ma, Xiao-Pan,Liang, Cui,Mo, Dong-Liang
, p. 3232 - 3238 (2017/03/23)
An efficient selective N-arylation of 3-(hydroxyimino)indolin-2-ones with diaryliodonium salts to prepare (Z)-N-aryl oxindole nitrones has been achieved under simple base-mediated conditions. The reaction tolerated a variety of diaryliodonium salts with diverse and sensitive functional groups. Studies on the oxime structures revealed that the pyrroline ring and carbonyl group in 3-(hydroxyimino)indolin-2-ones played important roles in the selective N-arylation process. The N-aryl oxindole nitrones could be prepared rapidly and easily at the gram scale.
Metal-free synthesis of isatin oximes: Via radical coupling reactions of oxindoles with t -BuONO in water
Wei, Wen-Ting,Zhu, Wen-Ming,Ying, Wei-Wei,Wu, Yi,Huang, Yi-Ling,Liang, Hongze
supporting information, p. 5254 - 5257 (2017/07/10)
A metal-free method for the synthesis of isatin oximes was developed through the radical coupling reactions of oxindoles with t-BuONO. This protocol provides a practical and environmentally benign method for the construction of C-N bonds in water at room temperature without using any other reagents. The advantages of this strategy are its mild reaction conditions and clean procedure.
A isatin - 3 - oxime derivatives of the preparation method (by machine translation)
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Paragraph 0023-0029, (2017/10/07)
The invention discloses a isatin - 3 - oxime derivatives of the preparation process, the method to 2 - indolone derivatives as raw materials, the water as a solvent, and nitrous acid tert-butyl at room temperature and under the condition of air reaction to obtain high yield and purity of the isatin - 3 - oxime derivatives. The method of the invention does not use the metal reagent, with synthetic and post treatment process is simple, low cost, environment-friendly advantages. (by machine translation)
